Sulfuric Acid → 8-Methoxy-3-methylquinoline

HRID 1167186Notes

Reaction equation

HRID 1167186 reaction equation
S(=O)(=O)(O)O.[CH3:6][O:7][C:8]1[C:9]([NH2:14])=[CH:10][CH:11]=[CH:12][CH:13]=1.O=[CH:16][C:17](=[CH2:19])[CH3:18].C(=O)([O-])[O-].[Na+].[Na+]>[I-].[Na+].O>[CH3:19][C:17]1[CH:16]=[N:14][C:9]2[C:10]([CH:18]=1)=[CH:11][CH:12]=[CH:13][C:8]=2[O:7][CH3:6]

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 6562MethacroleinHCID 70002-MethoxyanilineHCID 10340Sodium Carbonate

Product 1

HCID 139842868-Methoxy-3-methylquinolineYield 29.5%

Reagents, catalysts & solvents 2

HCID 5238Sodium IodideCatalystHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

94 ml of concentrated sulfuric acid and 70 ml of water are placed in a 1 l triple-necked flask equipped with a mechanical stirrer. The mixture is cooled to 0° C. with an ice bath and the dropwise addition is carried out of 45 g (366 mmol) of ortho-anisidine, followed by 0.54 g of sodium iodide. The mixture is then heated with an oil bath to 115° C. and 50 ml (604 mmol) of methacrolein are added using a syringe driver at the rate of 25 ml/h. Heating is continued for 1 h after the addition. The mixture is cooled to ambient temperature and then thrown onto a mixture of ice and of sodium carbonate. Extraction is carried out with dichloromethane. The organic phases are combined, dried over magnesium sulfate, filtered and evaporated under vacuum. The residue is purified by silica gel chromatography (eluent: dichloromethane/methanol 98/2) to provide 18.7 g of 3-methyl-8-methoxyquinoline. (Yield: 29.5%)

Workup

  1. customequipped with a mechanical stirrer
  2. additionthe dropwise addition
  3. temperatureThe mixture is then heated with an oil bath to 115° C.
  4. temperatureHeating
  5. additionafter the addition
  6. temperatureThe mixture is cooled to ambient temperature
  7. extractionExtraction
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. customevaporated under vacuum
  11. customThe residue is purified by silica gel chromatography (eluent: dichloromethane/methanol 98/2)

Sources & evidence

ORD record
ord-ca789576c5e543ae9d79d459a2376a0a
Source dataset
uspto-grants-2003_09
Patent number
US06617336B1

Reaction notes

Loading…